Oars, are cheap and will always work. We rowed for a year, even up to a mile from shore, instead of using a motor because we had oars and we didn’t want to have the expense of a motor. In the Bahamas, we salvaged an air-cooled Honda 2hp outboard and began using that to power the dinghy.
What we learned from this is that oars work just fine, but an outboard motor is nice! You can get places quickly, and you can go at any time you want without waiting for slack water.
Don’t stock up on food when you start cruising
I made this mistake. I thought that I was going to leave Baltimore where I had several grocery stores around me, and set off into the desert of a world with no places to buy food. I needed to have a lifetime supply of canned food on the boat so that I wouldn’t starve to death!
Everyone eats, and if you need food, go to the grocery store. There are these really cool devices called smart phones where you can search for grocery stores near you, and I can assure you there is always one within walking distance from any civilized anchorage.
One of my favorite places to anchor out was Harness Creek on South River. I liked it because I felt like I was “so removed” from society. There are a few mansions on the water and then trees forever! The place feels like you have been teleported to a new world and civilization is gone. Yeah, we were anchored in there for a few weeks when we started cruising and there is a grocery store about 15 minutes away from the anchorage.
Don’t do a big grocery run before you go, just untie the lines and be happy. When you run out of food, go ashore and get some more.
Don’t stay in the same state
Each state has it’s own flavor of cruising, and this is very apparent based on the laws that govern the waterways. Maryland is a state where the property line is dictated by the high tide water mark. This means that at high tide, there is no public land to walk on by a house. At low tide, all the land that has been uncovered is public (and you can walk your dog here legally).
Virginia sets the property line based on the low tide mark, meaning that there is no public land in front of a house. Maryland and Virginia also don’t have much in the way of public piers or good shore access from the water. It almost feels like they don’t want people living aboard in their waters. If you are in these areas, consider finding a mooring field to live in, as this gives you some rights when a land owner complains and the marine police come and start hassling you.
North Carolina is the most friendly state in our opinion. Everywhere we went, there would be wonderful free docks for us to tie up our dinghy and come ashore. The towns almost wanted us to come ashore and spend our money on groceries, meals, and supplies!
South Carolina was almost as inviting, but the dinghy docks required a fee.
Florida, while people talk about them cracking down on anchored boats, seemed really cruiser friendly! They had many free docks where we could tie up, even with free buses that would make stops right at the free dock! The boats that seemed to get hassled were the derelict looking boats, you know, the ones that you see listed on Craigslist for FREE. We take pride in our boat and make sure she always looks spiffy when she is anchored and we never had any problems with the police while we were anchored. That said, we did see the policy “check on” a dismal looking boat that was anchored next to us. The owner of the boat would yell at the police to “stop harassing him” which would usually lead to a morning show in the anchorage.
Keep your boat looking nice
You are judged by your boat. If your boat looks like a dump, people won’t want you near their stuff. They will fear that you are going to steal stuff and will frequently call the police on you. If your boat looks nice and you make yourself look presentable, people will usually invite you over for a meal and will want to get to know you! Appearances are what you are going to be judged on, and first impressions really matter.
Get an education
Educations come at a price. The price tends to be insane student debt but the result is the ability to land a job that you can work and go cruising. I went to college from 2004 to 2008, then dental school from 2008 to 2012. I graduated with a hefty sum of student debt.
The result is I earn enough money when I work to afford to buy items for the boat. This means that I can afford a nicer boat and it doesn’t look like a homeless person living in a free boat. This also means that I can work for a short period of time and afford to go cruising for an extended amount of time.
While we were cruising, we came across many many cruisers in the ICW. It seemed that there were two categories: No education and educated. The ones with no education were in 20-some footers with tarps over the boom (also called the liveaboard tent) and had no money for anything. Police frequently badgered these cruisers because the locals would complain about them. When these people pulled into port, the locals knew they had no money and were not going to offer anything to the town, but instead feared that they might rob from the townies. These people were all very nice and would not commit such forms of crime, but they were broke and they couldn’t afford to experience the towns they stopped in.
The educated people would show up on boats that were larger and much nicer. The boats were well cared for and the locals would welcome these people into their towns. Our interactions with police were always pleasant and usually involved them giving us advice on things to see in the town or places to eat! Having a degree also helps if anyone questions who you are or what you are doing. We arrived in one town after dark and were trying to find a (cheap) restaurant to eat in. A local saw us looking around the town and asked us what we were up to. At first they seemed suspicious and rather defensive, but once I introduced myself as Dr. So-and-so, they became totally relaxed and actually helped us find a great local restaurant that was still open!
Don’t wait
I waited for 5 years to go cruising because I always thought of another thing I needed to do before I could untie the lines and go. Truth is, the boat is still not ready to go and we have crossed an ocean! Once you have the basics (good ground tackle, good steering, good rigging, good sails) you are ready to go!